1. Field of the Invention
The present invention relates to a cucurbituril-containing polymer, a stationary phase and a column using the same. The present invention relates to a cucurbituril-containing polymer, a stationary phase and a column using the same. More particularly, the present invention relates to a cucurbituril-bonded polymer, a cucurbituril derivative-containing copolymer, a stationary phase and a column using the polymer or the copolymer, which are useful for separation and removal of substances.
2. Description of the Related Art
Generally, a column packing material is a material that is used as a stationary phase upon separation and purification of various test samples. Various column packing materials in which various compounds are bonded to silica gels have been developed as stationary phases. Crown ether (Korean Patent No. 0263872) and cyclodextrin (U.S. Pat. No. 4,539,399) are known as a representative material bonded to a silica gel. A silica gel bonded with crown ether or cyclodextrin is used as a stationary phase in separation of various test samples by selective non-covalent interactions with various organic or ionic compounds.
Like cyclodextrin, it is known that cucurbituril has retention capacity for various compounds due to the presence of hydrophilic and hydrophobic cavities. However, unlike cyclodextrin, cucurbituril has carbonyl groups on the entrance of the cavities, and thus, can retain various ionic compounds and high polarity compounds by charge-polarity interactions, polarity-polarity interactions, or hydrogen bonds. Therefore, cucurbituril has retention capacity for various compounds, for example, organic compounds such as gaseous compounds, aliphatic compounds, and aromatic compounds, insecticides, herbicides, amino acids, nucleic acids, ionic compounds, metal ions, or organic metal ions (J. Am. Chem. Soc. 2001, 123, 11316; European Patent No. 1094065; J. Org. Chem. 1986, 51, 1440). However, there exist few solvents capable of solubilizing cucurbituril. Furthermore, cucurbituril contains no substituents, and thus, has an extremely limited application, such as a covalent linkage with solids such as silica gel or polymers.
An example of utilization of cyclodextrin-containing polymer as a stationary phase is reported (U.S. Pat. No. 5,403,898). A stationary phase based on such cyclodextrin-containing polymer can be used in separation of various water-soluble compounds by reverse-phase column chromatography (U.S. Pat. No. 5,516,766). However, as described above, since cyclodextrin has weaker non-covalent binding capacity with various biochemical substances or ions, relative to cucurbituil, its utility is limited.
Recently, there has been an increasing interest in a monolithic column due to its more efficient and rapid separation capacity (U.S. Pat. No. 6,398,962). However, no cucurbituril derivatives have been reported until recently, and thus, there are no studies about preparation of monolithic columns using cucurbituril.
International Patent Application No. PCT/DE02/01980 discloses a silica gel physically coated with cucurbituril prepared by adding the cucurbituril and silica gel to a solvent followed by thermal treatment. However, since the physical coating is not covalent-binding, there are limitations for reproducibility and chemical and physical stability. International Patent Application No. PCT/KR02/02213 discloses a method for preparing hydroxycucurbituril. This method can overcome the above-described disadvantages of cucurbituril. Hitherto, however, there are no reports about separation of various water-soluble substances on a reverse-phase column containing a polymer covalently bonded with cucurbituril derivative.